Apple iPhone 15 Pro Max: Transition Blockers and Delays

It felt like the whole world conspired against me this past week, preventing me from migrating to the iPhone 15 Pro Max. But I finally got it done. It’s just that the process took five days longer than I had originally hoped.

I’m reminded of the oft-repeated quip that Jerry Pournelle would make in BYTE Magazine back in the day, “I make mistakes so you don’t have to.” My version of that is, “I make mistakes because I can be an idiot, but hopefully you can still learn from them.” With that little adage in mind, my problems this past week predate this past week. That is, I made some changes to my iPhone 15 Pro Max order between the time I made it and when I received the phone. Not to the phone itself, but rather to the peripherals I ordered along with it. And there was some user error involved.

As you may recall, at the time of my preorder, I had added an Apple FineWoven Case with MagSafe in Evergreen, a 20-watt USB-C power adapter, and a 60-watt USB-C charging cable to the basket, bringing my total purchase price to a gulp-inducing $1382.24 after taxes and shipping. But with a lot of lead time, I was able to read and watch some reviews, and so I made some changes. I returned the FineWoven case because they’re so horrible, and then I ordered a similarly-colored silicone case to replace it. And because this iPhone can charge at up to 30 watts, I also returned the Apple power adapter, did 10 seconds of research, and purchased an Anker 30-watt Nano 3 power adapter from Amazon.

Of course, the iPhone arrived more quickly than expected, which is nice for all the obvious reasons, but also because it would give me more time with the device before Google launches the Pixel 8 Pro. But it also arrived before my replacement case did, preventing me from switching my eSIM over to it because I refuse to bring this expensive, fragile, and slippery trinket out into the world without a case. And when the case did arrive just a day later, I figured, great, I’m good to go. But I wasn’t. I had mistakenly ordered a (non-Max) iPhone 15 Pro silicon case for my Max. Not the Max case.

Doy. So I set up a second case for return and then ordered a Pro Max case instead. Which was set to arrive on Thursday, three days after I got the iPhone. And we will rule this error to the fielder, so to speak. Meaning me.

Even with all the returns and exchanges, the total price of this purchase didn’t change because Apple’s cases all cost the same, and the Anker power adapter is the same price as Apple’s. So assuming I get my full $480 trade-in value for the iPhone 13 Pro—which I still haven’t reset and sent in; I have a total of 14 days to do so—the final tally will still land at around $900. Which, yes, is a lot of money, but not much higher than the average cost of a smartphone in the U.S. (which is about $823 right now).

So that was the first blocker.

Then the proper case finally did arrive, and on schedule, and so I was able to protect the iPhone 15 Pro Max, set up that eSIM, and take it for its first excursions out in the world. Is what I wish I could write. But as it turns out, life wasn’t done messing with me.

The case arrived late Thursday afternoon, which seems to be the normal UPS schedule at our apartment, when I was busy writing up my latest digital decluttering post, an unintended magnum opus that I had hoped to keep to a much shorter length. And so I popped on the case but left the iPhone next to me while I finished working past dinner. During this time, I searched for and found a hero image, took and then resized some screenshots, and re-read the whole thing yet again in WordPress while using the Grammarly extension for another grammar pass. The usual, for sure, but it was getting late.

This was the second blocker: this past week, like the previous week, was incredibly busy from a work perspective. And by the time Friday was winding down, I was wiped. But while I was finishing up that article, I kept looking over at the iPhone, and kept thinking about the terrible, lengthy process I always go through on T-Mobile because I have to call or chat with a customer support representative and was dreading that. And then I remembered that a few readers had commented in my first impressions post that they were T-Mobile customers and never needed to do that, that their experience was the normal one: Just set up the eSIM yourself and go. And I started to get distracted. Maybe T-Mobile finally reverted back to the normal way of doing things. After all, this was supposed to be temporary. And if so, I could just activate the iPhone and get going with it.

And so I picked up the iPhone, ignoring the final steps of publishing that post for a moment, and tried to just activate the eSIM like a normal person. And what I saw when I went into Cellular settings was that there were two inactive eSIMs configured, one for my T-Mobile account and one for my Tel-Mex account. These had been configured previously on my iPhone 13 Pro, and so when I upgraded this phone it had obviously pulled them both over. That the Tel-Mex SIM was a physical nano-SIM and almost certainly wouldn’t work as an eSIM was no problem, I could just move that SIM to another phone (one that supports physical SIMs). I was more interested in the T-Mobile account.

And … it did not work. It’s possible that it might have worked if I had been using it actively on my previous iPhone at the time of the transfer, I’ll never know. But back in March, I switched the eSIM from the iPhone 13 Pro to my Pixel 7 Pro and have been using it there ever since. So I’m not surprised it didn’t work. But I was surprised that there was no way in the Settings UI to change the configuration of either eSIM. Or, ominously, delete either one and just start over. Both were just marked as “used” and “NO SIM.”

So I installed the T-Mobile app on my new iPhone, which was connected to just the Wi-Fi, and contacted support using chat. After a long wait, I was connected to a human, waited, provided them the requested EID and IMEI numbers, waited, and was finally told that I should see a message on the iPhone confirming the successful eSIM switch. I did not see this, so I waited. And got worried.

And then it occurred to me: I had inadvertently introduced yet another blocker.

As you may recall, I always do a clean install on my phones, but for some reason, I decided to have the normal experience this time and I did what I assume most people do by letting it upgrade from the previous iPhone, what I think of as an upgrade. This was why my previous iPhone’s eSIM configuration was already on there. A quick Google search landed me on an Apple Support page that verified my fear: There was nothing T-Mobile could do to fix this issue and correctly configure the eSIM. As one commenter to that support thread noted, “This is on Apple.”

Sigh.

I explained to the customer service rep that I would be resetting the phone, not their fault, and that I would contact them again later. And then I did just that, blowing away the upgrade configuration that I had stupidly allowed this past Monday and finally doing what I should have done in the first place. As I did this, the tragic waste of time this triggered occurred to me: Because of my case fiasco, I had delayed setting this thing up completely for three days. But now I would delay that further because I was resetting it. If I had just done what I usually do, it would have been good to go.

For all the mistakes, one thing did work, and unexpected: When the iPhone 15 Pro Max came back up, the cellular signal connected immediately during setup. The “push” that T-Mobile had made prior to the factory reset had somehow taken regardless. I raced through setup to make sure it was OK, positive that I would be spending more time with T-Mobile support Thursday night. But it worked. I exchanged text messages and a phone call with my wife, and it was fine. Thank God.

It was also almost 8:30 pm by this point and the two of us usually start watching TV at 8:00 pm. I had explained the stupidity I was enduring with T-Mobile to my wife earlier, and as the night’s activities unfolded, that we’d be starting late. And so when I finally sat down to get through a bit of middling binge TV (Night Agent on Netflix, about as unexceptional as it gets), I told my wife that I’d have to sit there and install and configure apps so I could be ready to roll in the morning. No worries. And by the time we had gotten through two episodes were past ready for bed, the iPhone was in a pretty good place.

And as promised a million words ago, I finally did take it for its first excursions out in the world, this morning, during our daily 40-minute walk. Unfortunately, it was gloomy and overcast this morning, and we left a little bit late—we usually get back just in time for First Ring Daily on weekdays so time was of the essence—and so I wasn’t able to take as many pictures as I had hoped. But still, it was finally happening. I just had a few configuration tasks to complete, one of which was quite important.

Friday was busy, it always is, but by mid-afternoon, I was starting to think about the next steps for the iPhone. There was one major issue hanging over my head, my Microsoft Authenticator app. Over the past year, I’ve added more and more accounts to this 2FA system on my Pixel, and redoing them all manually on a new phone is a tedious slog. But I was hoping that there was some backup/restore system that would work across the platforms, saving me from this.

There is not. Yet another blocker.

As it turns out, you can only restore from a Microsoft Authenticator backup on the same platform. And that I meant I had to re-do every single account I use, one by one, on the iPhone. That took about two hours. And by the time my wife asked me when we were leaving for dinner Friday night, at 5:30 p.m., I was literally just wrapping that up. Tedious. But off we went. At least I was done.

Two notes related to passwords and authentication.

First, I did investigate replacing Microsoft Authenticator with the new Google Authenticator app because the latter supports account sync, which means that you can bring all your stored accounts between platforms, and probably pretty easily. (And, yes, I know that this app currently lacks end-to-end encryption, though that feature is coming.) The problem is that (consumer) Microsoft accounts (MSAs) and Microsoft Work and School accounts don’t work seamlessly in Google Authenticator because these accounts use a number-matching feature that the latter app does not support.

Second, iOS 17 has a new option in Password settings that will automatically delete verification codes in Messages and Mail after you insert them with AutoFill. Thanks to authenticator apps, these types of 2FA verification are less common now, but it’s a nice thing to enable. (Google Messages offers a similar feature on Android.)

I at least had some reasonable test shots by this point, helping me understand the iPhone’s camera system, which is mostly pretty familiar. The goofy multi-tap main lens button in the Camera app is, well, goofy, and I doubt I’ll leave that enabled. The pictures, generally speaking, are very good, but I need more examples to be sure. Anyway, here are a few test shots.

By Saturday morning I was ready to wrap things up. The next (final?) steps were to configure notifications on the new iPhone while simultaneously copying the files from my old iPhone to a PC so I could then archive them on the NAS, wipe out the old iPhone, and ship it back to Apple and get its trade-in value removed from my bill.

Configuring notifications entails turning off all the unnecessary notification pop-ups and sounds. And to be clear, iPhone notifications are terrible. (For all the pros and cons of iPhone vs. Pixel, this one is quite one-sided. And in Pixel’s favor.) But you go to war with the army you have, and I did just install dozens and dozens of apps, all of which are now vying for my attention. (Seriously, some of them are insane by default, triggering multiple notifications each day.) And rather than spend the next week reactively configuring notifications on an app-by-app basis as they occurred, I figured I could be proactive and configure this system as much as possible to my liking.

And I wish this was better.

For example, I would ideally be able to disable all notification sounds globally and then enable them in only the small number of apps—Phone, Messages, maybe some messaging apps—where sound is desirable. But that’s not how this works. On the iPhone, there are Notifications settings and Sounds & Haptics settings, and after a bit of back and forth, I realized the latter was useful for this task and that I’d have to individually configure notifications for every single app I had installed on the phone. And this means that reacting to notifications as they arrive may, in fact, be the most efficient choice. Assuming I can live with the triggering sound of unnecessary notification sounds for the next week or whatever. Another blocker.

There is all kinds of weirdness to this system. For example, I had configured the Amazon app’s notifications as I preferred the first time it trilled its unnecessary sound and lit up my iPhone’s always-on display with a pop-up. And now it reports that its notification style is “Deliver Quietly.” Which is neat, except that there is no “Deliver Quietly” choice in Notifications settings. Instead, you get this title when you configure an app to not display banners, sounds, and badges, and, yes, you have to configure each one of those options for every single app where this is the case. On and on it goes.

Some apps, granted, are easy to configure. If you just don’t want any notifications, here’s a single switch for that. But it’s still a per-app thing.

This system makes me crazy. And for many reasons beyond configuration. For example, when there’s a pending notification for an app, its home screen icon will display a red dot (a badge) to let you know. On Android, you can press and hold on that app icon (like right-clicking) and see and deal with the pending notifications right from the pop-up menu that appears. But on iPhone, you cannot. You have to open the app. Come on Apple, learn from Google. You’ve done it in the past.

While I was struggling with this, I had connected the old iPhone to my desktop PC via a USB-to-Lightning cable so I could copy the contents of its “Internal Storage” folder to the PC and then archive it to the NAS. But it would never successfully copy; it just quietly quit part way through again and again. I literally babysat this thing all morning and never got it to work, and so I eventually just copied the folders over in smaller groups. And that finally did work. At 1:30 pm, many hours after I had expected to complete this copy, reset the iPhone, clean it up and pack it, and probably even bring it to FedEx, all I had done was replicate the iPhone’s contents on my PC. Well, at least it finally worked.

Except that it didn’t. I always check the properties of the source and destination on a copy like this to ensure that the total size and number of files are the same on each. And the iPhone (slowly, f#$%ing Lightning) reported that it had 6 GB of data on there, while the copy on the PC was … 21 GB. What the what.

Yep. Another blocker.

Finally, I just tried another PC. Same slowness, of course. But this time, as I compared the relative sizes of each batch of folders, I got identical values each time. I have no idea what happened with the other PC, all I know is that I wasted hours and hours trying to make it work. Aggravating.

As I write this, the file copy is still ongoing. But it’s working. And when my old iPhone 13 Pro is finally backed up to the NAS, I will reset it and package it up for return. The device is in great shape, in part because it’s always been protected by a case, and it served me well enough during the on-again-off-again times I used it. That said, I will not miss its small display and Lightning port. Good riddance.

And now I can finally just use the iPhone 15 Pro Max. You know, like a semi-normal person.